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Movies like Free Rein: Valentine's Day (2019)

The best movies like Free Rein: Valentine's Day (2019) are It Was Always You (2021), Holiday Date (2019) and All of My Heart: The Wedding (2018). If Free Rein: Valentine's Day hooked you with its romance and family, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. It Was Always You (2021)

    Elizabeth's engagement plans are thrown into disarray when her fiancée's free-spirited brother David returns home. David's unexpected influence prompts Elizabeth to question her life decisions.

    Why it matches: Recommended by TMDB viewers · both romance

    Worth the HypeMovies like this
  2. Holiday Date (2019)

    When Brooke’s boyfriend, Ethan, breaks up with her just before the holidays, she agrees to go home with Joel, an actor who will pose as her boyfriend.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  3. All of My Heart: The Wedding (2018)

    Brian and Jenny are planning their wedding at the Inn where they fell in love. When a distant relative arrives and stakes their claim to the Inn, Brian and Jenny must find a way to save their beloved Inn or risk having to sell.

    Why it matches: Recommended by TMDB viewers · both romance

    Worth the HypeMovies like this
  4. Sailing Into Love (2019)

    A biology teacher’s crusade to save a nearby island from development leads to unexpected romance with the handsome and mysterious young sea captain who is new to the seaside town of Willow Bay.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  5. Brigadoon (1954)

    Americans Jeff and Tommy, hunting in Scotland, stumble upon a village - Brigadoon. They soon learn that the town appears once every 100 years in order to preserve its peace and special beauty. The citizens go to bed at night and when they wake up, it's 100 years later. Tommy falls in love with a beautiful young woman, Fiona, and is torn between staying or going back to his hectic life in New York.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  6. Nancy Drew and the Hidden Staircase (2019)

    Nancy Drew, a smart high schooler with a penchant for keen observation and deduction, stumbles upon the haunting of a local home. A bit of an outsider struggling to fit into her new surroundings, Nancy and her pals set out to solve the mystery, make new friends, and establish their place in the community

    Why it matches: Recommended by TMDB viewers · both family

    Popcorn FlickMovies like this
  7. The Secret of Moonacre (2009)

    When 13 year old Maria Merryweather's father dies, leaving her orphaned and homeless, she is forced to leave her luxurious London life to go and live with Sir Benjamin, an eccentric uncle she didn't know she had, at the mysterious Moonacre Manor.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  8. A Fairy Tale After All (2022)

    A stubborn teenage girl finds herself confronted by whimsical characters when she is transported into a world of fantasy and fairy tales while attending a school marionette show.

    Why it matches: Recommended by TMDB viewers · both family

    Popcorn FlickMovies like this
  9. Anastasia: Once Upon a Time (2020)

    Anastasia Romanov escapes through a portal when her family is threatened by Vladimir Lenin, and she finds herself in the year 1988, befriended by a young American girl.

    Why it matches: Recommended by TMDB viewers · both family

  10. White Fang 2: Myth of the White Wolf (1994)

    A boy and his dog, White Fang, must try to save the noble Haida tribe from evil white men in turn-of-the-century Alaska.

    Why it matches: Recommended by TMDB viewers · both family

    Popcorn FlickMovies like this
  11. Love in the Forecast (2020)

    After swearing off dating for a full year, Leah quickly learns her new commitment has made her a magnet for men.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  12. Hansel and Gretel (1988)

    Hansel and Gretel tells the tale of two young children driven from home by their scolding mother. Losing their way in the dark forest they stumble upon the cottage of a kindly old woman. But is this kindly old woman everything she seems...?

    Why it matches: Recommended by TMDB viewers · both family

    Worth the HypeMovies like this
  13. Momo (2025)

    Momo is a young orphan girl who lives in the ruins of an old Roman amphitheater and becomes friends with everybody in the neighborhood. But when a powerful international corporation starts stealing everybody’s time, nobody has any time left for her, let alone their friends or families. Momo, together with Master Hora, the custodian of time, are the only ones who can go up against the time thieves before all is lost forever.

    Why it matches: Recommended by TMDB viewers · both family

    Worth the HypeMovies like this
  14. Four Kids and It (2020)

    A group of kids on holiday in Cornwall meet a magical creature on the beach with the power to grant wishes.

    Why it matches: Recommended by TMDB viewers · both family

    Popcorn FlickMovies like this
  15. The Dirt Bike Kid (1985)

    When his mother sends Jack off with money to buy groceries, he comes home with a magic supercharged dirt bike instead. His mother is furious, but when Jack uses the magic bike to save the local hot dog stand from the clutches of corrupt big business, he becomes the town hero.

    Why it matches: Recommended by TMDB viewers · both family

    Popcorn FlickMovies like this
  16. Winter Love Story (2019)

    When new author Cassie is paired with successful author Elliot on a promotional book tour, she learns to believe in her talent. She also finds truth in the old adage “you can’t judge a book by its cover” as she falls for the guy she once thought to be pompous and full of himself.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  17. Midnight Masquerade (2014)

    Young businesswoman Elyse Samford's life takes a turn when she inherits Samford Candy, a multi-billion dollar corporation, from her retired father. A trademark infringement lawsuit against a rival company brings Elyse to Higgins Attorneys and Sons, where Rob Carelli, a young, too-nice-for-his-own-good lawyer, is bullied by his boss, firm founder Carter Higgins, and his two arrogant sons. Despite his workplace woes, Rob becomes instantly smitten with Elyse. With Halloween just around the corner, Elyse invites the Higgins law firm staff to an opulent masked Halloween costume ball. Rob obeys an order to remain in the office working that night, but has a change of heart when his spunky, 12-year old niece Ruby, convinces him to attend the ball wearing a prince costume. After a magnificent waltz and magical exchange with the handsome "prince," Elyse yearns to locate this mysterious man and hopefully find the romance her life has been missing.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  18. Marry Me at Christmas (2017)

    Organizing a Christmas wedding is a true treat for bridal boutique owner Madeline Krug. She loves the challenge of finding the perfect dress for the bride and orchestrating an exquisite event. What Madeline didn’t expect was to be swept off her feet by the bride’s gorgeous brother, movie star, Jonny Blaze. Jonny came to the quirky town of Fool’s Gold to support his sister -- not to fall in love. Yet Madeline is the most extraordinary woman he’s ever met, and she finds the real Jonny even more captivating than her celebrity crush. Will the action star be brave enough to take on the role of a lifetime?

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  19. PAW Patrol: Jet to the Rescue (2020)

    A royal relative steals a gem with the power to make things fly, the Paw Patrol takes to the skies to stop him and save Barkingburg.

    Why it matches: Recommended by TMDB viewers · both family

    Worth the HypeMovies like this
  20. Chateau Christmas (2020)

    Margot, a world-renowned pianist, returns to Chateau Newhaus to spend the holidays with her family and is reunited with an ex who helps her rediscover her passion for music.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this

Like Free Rein: Valentine's Day and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like Free Rein: Valentine's Day?

The closest matches to Free Rein: Valentine's Day are It Was Always You (2021), Holiday Date (2019) and All of My Heart: The Wedding (2018). Below are 17 more, each with the reason it matches.

What should I watch after Free Rein: Valentine's Day?

Start with It Was Always You (2021), the closest match to Free Rein: Valentine's Day.

What is the highest-rated movie like Free Rein: Valentine's Day?

The Secret of Moonacre (2009), rated 6.6/10 by 519 TMDB users.

What is the newest movie like Free Rein: Valentine's Day?

Momo (2025) is the most recent release on this list.

Are there English movies like Free Rein: Valentine's Day?

Yes: It Was Always You (2021), Holiday Date (2019) and All of My Heart: The Wedding (2018).

How are movies similar to Free Rein: Valentine's Day chosen?

First come films that Trakt’s viewers watch alongside Free Rein: Valentine's Day, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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